Abstract:
Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO3/H+) and neutral conditions (Cu(NO3)2; ceric ammonium nitrate) are discussed. A complete 1H and 13C-nmr characterization including ms and also uv absorption spectra in neutral and acid media is presented. A detailed ei-ms and ld-tof-ms study is enclosed because the nitro-β-carbolines constitute a new family of β-carboline-like chromophores with potential use as matrix in uv-maldi-tof-ms.
Registro:
Documento: |
Artículo
|
Título: | Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids |
Autor: | Ponce, M.A.; Erra-Balsells, R. |
Filiación: | Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina
|
Palabras clave: | ammonium nitrate; beta carboline; carboline derivative; carbon 13; copper derivative; harman; harmine; harmol; harmol derivative; unclassified drug; article; drug isolation; drug synthesis; light absorption; nitration; nuclear magnetic resonance spectroscopy; proton nuclear magnetic resonance; reaction analysis; ultraviolet spectroscopy |
Año: | 2001
|
Volumen: | 38
|
Número: | 5
|
Página de inicio: | 1071
|
Página de fin: | 1082
|
DOI: |
http://dx.doi.org/10.1002/jhet.5570380510 |
Título revista: | Journal of Heterocyclic Chemistry
|
Título revista abreviado: | J. Heterocycl. Chem.
|
ISSN: | 0022152X
|
CODEN: | JHTCA
|
CAS: | ammonium nitrate, 6484-52-2; beta carboline, 244-63-3; carbon 13, 14762-74-4; harman, 486-84-0; harmine, 343-27-1, 442-51-3; harmol, 487-03-6
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v38_n5_p1071_Ponce |
Referencias:
- Marion, L., (1952) The Alkaloids, 2. , eds. R. H. Manske and H. L. Holmes, Academic Press, New York
- Allen, J.R.F., Holmstedt, B.R., (1980) Phytochemistry, 19, p. 1573
- Towers, G.H.N., (1984) Can. J. Bot., 62, p. 2900
- Sen, A.C., Ueno, N., Chakrabarti, B., (1992) Photochem. Photobiol., 55, p. 753
- Poindexter, E.H., Carpenter, R.D., (1962) Phytochemistry, 1, p. 215
- Schultes, R.E., (1969) Science, 163, p. 245
- Ho, B.T., McIsaac, W.M., Walker, K.E., Estevez, V., (1968) J. Pharm. Sci., 57, p. 269
- Müller, W.E., Fehske, K.J., Borbe, H.O., Wollert, U., Nanz, C., Rommelspacher, H., (1981) Pharm. Biochem. Behav., 14, p. 693
- Larson, R.A., Marley, K.A., Tuveson, R.W., Berenbaum, M.R., (1988) Photochem. Photobiol., 48, p. 665
- Hudson, J.B., Graham, E.A., Towers, G.H.H.N., (1986) Photobiol. Photochem., 43, p. 21
- Chae, K.H., Ham, H.S., (1986) Soc. Bull. Korean Chem., 7, p. 478
- Erra-Balsells, R., Frasca, A.R., (1983) Tetrahedron, 39, p. 33
- Muñoz, M.A., Carmona, C., Hidalgo, J., Guardo, P., Balon, M., (1995) Bioorg. Med. Chem., 3, p. 41
- Duportail, G., (1981) Int. J. Macromol., 3, p. 188
- Ghiggino, K.P., Skilton, P.F., Thistlethwaite, P.J., (1985) Pohtochem. J., 31, p. 113
- Pardo, A., Reyman, D., Poyato, J.M.L., Medina, F., (1982) J. Lumin., 42, p. 113
- Wolfbeis, O.S., Fuerlinger, E., Winstersteiger, R., (1982) Monatsh. Chem., 113, p. 509
- Wolfbeis, O.S., Fuerlinger, E., (1982) Z. Phys. Chem. N.F., 129, p. 171
- Tomas Vert, F., Zabala Sanchez, I., Olba Torrent, A., (1983) J. Photochem., 23, p. 355
- Tomas Vert, F., Zabala Sanchez, I., Olba Torrent, A., (1984) J. Photochem., 26, p. 285
- Tomas, F., Zabala, I., Olba, A., (1985) J. Photochem., 31, p. 253
- Biondic, M.C., Erra Balsells, R., (1990) J. Photochem. Photobiol., A: Chemistry, 51, p. 341
- Biondic, M.C., Erra Balsells, R., (1992) J. Chem. Soc., Perkin Trans. 2, p. 1049
- Biondic, M.C., Erra Balsells, R., (1993) J. Chem. Soc., Perkin Trans. 2, p. 887
- Biondic, M.C., Erra Balsells, R., (1994) Photochem. Photobiol., A: Chemistry, 77, p. 149
- Biondic, M.C., Erra Balsells, R., (1997) J. Chem. Soc., Perkin Trans. 2, p. 1323
- Biondic, M.C., Erra Balsells, R., (1998) J. Chem. Research (S), 27, p. 114
- Sakurovs, R., Ghiggino, K.P., (1982) J. Phytochem., 18, p. 1
- Dias, A.A., Varela, A.P., Miguel, M.D.G., Macanita, A.L., Becker, R.S., (1992) J. Phys. Chem., 96, p. 10290
- Draxler, S., Lippitsch, M.E., (1993) J. Phys. Chem., 97, p. 11493
- Balón, M., Hidalgo, J., Guardo, P., Muñoz, M.A., Carmona, C., (1993) J. Chem. Soc., Perkin Trans. 2, p. 99
- Nonami, H., Fukui, S., Erra-Balsells, R., (1997) J. Mass Spectrom., 32, p. 287
- Nonami, H., Tanaka, K., Fukuyama, Y., Erra-Balsells, R., (1998) Rapid Commun. Mass Spectrom., 12, p. 285
- Nonami, H., Orcoyen, M., Fukuyama, Y., Biondic, M.C., Erra-Balsells, R., (1998) An. Asoc. Quim. Argentina, 86, p. 81
- Iglesias, L.F., Fukuyama, Y., Baldessari, A., Erra-Balsells, R., Nonami, H., (1999) Biotech. Tech., 13, p. 923
- Eisenberg, P., Erra-Balsells, R., Ishikawa, Y., Lucas, J.C., Mauri, A.N., Nonami, H., Riccardi, C.C., Williams, R.J.J., (2000) Macromolecules, 33, p. 1940
- Williams, R.J.J., Erra-Balsells, R., Ishikawa, Y., Nonami, H., Adriana, N.M., Riccardi, C.C., (2001) Macrom. Phys. Chem., , in press
- Orgueira, H.A., Erra-Balsells, R., Nonami, H., Varela, O., (2001) Macromolecules, 34, p. 687
- Erra-Balsells, R., Kolender, A., Matulewicz, M.C., Nonami, H., Cerezo, A.S., (2000) Carb. Res., 329, p. 157
- Fritzsche, J., (1848) Justus Liebigs Ann. Chem., 68, p. 355
- Fritzsche, J., (1853) Justus Liebigs Ann. Chem., 88, p. 329
- Konovalova, R., Orekhov, A., (1935) Arch. Pharm., 273, p. 156
- Siddiqui, S., Ahmad, V.U., Khan, M.A., Ismail, S., (1973) Z. Naturforsh. B, 28, p. 486
- Snyder, H.R., Parmerter, S.M., Katz, L., (1948) J. Am. Chem. Soc., 70, p. 222
- Lomakin, A.N., Terent'eva, I.V., (1968) Khim. Geterotsikl. Soedin., p. 1041
- Shirshova, T.I., Terent'eva, I.V., Vember, P.A., Lazur'evskii, G.V., (1972) Chem. Heterocyclic Compound., 8, p. 898
- Muñoz, M., Balón, M., Hidalgo, J., Carmona, C., Pappalardo, R.R., Marcos, E.S., (1991) J. Chem. Soc., Perkin Trans. 2, p. 1729
- Sung, Y.-I., Koike, K., Nikaido, T., Ohmoto, T., Sankawa, U., (1984) Chem. Pharm. Bull., 32, p. 1872
- Saxena, J.P., (1966) Indian J. Chem., 4, p. 148
- Saxena, J.P., (1968) J. Indian Chem. Soc., 45, p. 628
- Carmona, C., Muñoz, M.A., Guardo, P., Balón, M., (1995) J. Phys. Org. Chem., 8, p. 559
- Ho, B.T., Li, K.-C., Walker, K.E., Wayne Tansey, L., Kralik, P.M., Mclsaac, W.M., (1970) J. Pharm. Sci., 59, p. 1445
- Hagen, T.J., Skolnick, P., Cook, J.M., (1987) J. Med. Chem., 30, p. 750
- March, J., (1992) Advanced Organic Chemistry, Reactions, Mechanisms, and Structures, 4th ed., 54, p. 4. , John Wiley and Sons, New York
- Smith, M.B., (1994) Organic Synthesis, , McGraw-Hill, Inc., New York
- Giziewicz, J., Wnuk, S.F., Robins, J.M., (1999) J. Org. Chem., 64, p. 2149
- Eckert, F., Rauhut, G., Katritzky, A.R., Steel, P.J., (1999) J. Am. Chem. Soc., 121, p. 6700
- Chakrabarty, M., Batabyal, A., (1994) Synthetic Communications, 24, p. 1
- Grossi, L., Strazzari, S., (2000) J. Org. Chem., 65, p. 2748
- Aulló, J.M., Tomas Vert, F., (1979) An. Quím., 75, p. 11
- Kyziol, J.B., Daskiewicz, Z., Hetper, J., (1987) Org. Mass Spectrom., 22, p. 39
- Coutts, R.T., Locock, R.A., Slywka, W.A., (1970) Org. Mass Spectrom., 3, p. 879
- (1998) HyperChem., , Suite, Autodesk, Inc., Ontario
- Frisch, J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pope, J.A., (1998) Gaussian 98W, Revision A.3., Gaussian 98, A.3, , Gaussian Inc., Pittsburgh PA
Citas:
---------- APA ----------
Ponce, M.A. & Erra-Balsells, R.
(2001)
. Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids. Journal of Heterocyclic Chemistry, 38(5), 1071-1082.
http://dx.doi.org/10.1002/jhet.5570380510---------- CHICAGO ----------
Ponce, M.A., Erra-Balsells, R.
"Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids"
. Journal of Heterocyclic Chemistry 38, no. 5
(2001) : 1071-1082.
http://dx.doi.org/10.1002/jhet.5570380510---------- MLA ----------
Ponce, M.A., Erra-Balsells, R.
"Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids"
. Journal of Heterocyclic Chemistry, vol. 38, no. 5, 2001, pp. 1071-1082.
http://dx.doi.org/10.1002/jhet.5570380510---------- VANCOUVER ----------
Ponce, M.A., Erra-Balsells, R. Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids. J. Heterocycl. Chem. 2001;38(5):1071-1082.
http://dx.doi.org/10.1002/jhet.5570380510